(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 86693334, compound

HRID 575302Notes

Reaction equation

HRID 575302 reaction equation
O[CH:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12.COCCN(S(F)(F)[F:32])CCOC>ClCCl>[F:32][CH:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86693328HCID 86693328, compound

Product 1

HCID 86693334HCID 86693334, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-hydroxy-9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate (400 mg, 1.00 mmol, 1.00 equiv) in dichloromethane (25 mL) was added [bis(2-methoxyethyl)amino]sulfur trifluoride (442 mg, 2.00 mmol, 2.00 equiv) at 0° C. After 4 h at room temperature the resulting mixture was washed with brine, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10). It resulted in 330 mg (82%) of the titled compound as a yellow solid. LC-MS (ES, m/z) 403 [M+H]+.

Workup

  1. washAfter 4 h at room temperature the resulting mixture was washed with brine
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10)

Sources & evidence

ORD record
ord-5be48c54907f4499b7a329d869ccf5d1
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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